Natural Product: NPC51662

Natural Product ID:  NPC51662
Common Name:   Nigericin
IUPAC Name:   (2R)-2-[(2R,3S,6R)-6-[[(2S,4R,5R,6R,7R,9R)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyloxan-2-yl]propanoic acid
Synonyms:   Nigericin
Molecular Formula:   C40H68O11
Standard InCHIKey:  DANUORFCFTYTSZ-SJSJOXFOSA-N
Standard InCHI:  InChI=1S/C40H68O11/c1-21-11-12-28(46-33(21)26(6)36(42)43)17-29-18-30(45-10)27(7)40(48-29)25(5)19-38(9,51-40)32-13-14-37(8,49-32)35-23(3)16-31(47-35)34-22(2)15-24(4)39(44,20-41)50-34/h21-35,41,44H,11-20H2,1-10H3,(H,42,43)/t21-,22-,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,37-,38-,39-,40+/m0/s1
Canonical SMILES:  CO[C@@H]1C[C@@H](C[C@H]2CC[C@@H]([C@@H](O2)[C@H](C(=O)O)C)C)O[C@@]2([C@@H]1C)O[C@](C[C@H]2C)(C)[C@H]1CC[C@@](O1)(C)[C@@H]1O[C@H](C[C@@H]1C)[C@H]1O[C@@](O)(CO)[C@@H](C[C@@H]1C)C
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO13391 Streptomyces hygroscopicus Species Streptomycetaceae Bacteria StreptomeDB*
NPO9685.9 Streptomyces violaceusniger yced9 Subspecies Streptomycetaceae Bacteria StreptomeDB*
NPO22810 Streptomyces Species Streptomycetaceae Bacteria StreptomeDB*
NPO17794 Streptomyces violaceusniger Species Streptomycetaceae Bacteria StreptomeDB*
NPO32206 Streptomyces prh5 Species Streptomycetaceae Bacteria StreptomeDB*
NPO31899 Streptomyces rja2926 Species Streptomycetaceae Bacteria StreptomeDB*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1892 Cell Line H4 Rattus norvegicus Activity = 551.04 % 18024584
NPT1892 Cell Line H4 Rattus norvegicus Activity = 747.88 % 18024584
NPT1892 Cell Line H4 Rattus norvegicus Activity = 375.67 % 18024584
NPT1892 Cell Line H4 Rattus norvegicus Activity = 148.43 % 18024584
NPT1892 Cell Line H4 Rattus norvegicus Activity = 145.4 % 18024584
NPT1892 Cell Line H4 Rattus norvegicus Activity = 140.54 % 18024584
NPT1892 Cell Line H4 Rattus norvegicus Activity = 106.9 % 18024584
NPT1892 Cell Line H4 Rattus norvegicus Activity = 91.75 % 18024584
NPT1892 Cell Line H4 Rattus norvegicus Activity = 88.14 % 18024584
NPT1892 Cell Line H4 Rattus norvegicus Activity = 96.9 % 18024584
NPT1892 Cell Line H4 Rattus norvegicus Activity = 95.98 % 18024584
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 6 nM 11430019
NPT759 Cell Line H9 Homo sapiens IC50 = 140 nM 11430019
NPT32 Organism Mus musculus Mus musculus LD50 = 10 mg/kg 3819734
NPT3130 Organism Lepidium sativum Lepidium sativum Activity = 50 % 3819734
NPT984 Cell Line Hepatocyte TC50 = 1.32 nM 18212104
NPT1188 Organism Plasmodium yoelii yoelii Plasmodium yoelii yoelii IC50 < 0.001 nM 18212104
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 < 0.001 nM 18212104

  Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC51662 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9518 High Similarity NPC314364
0.8395 Intermediate Similarity NPC138273
0.8293 Intermediate Similarity NPC228411
0.814 Intermediate Similarity NPC477347
0.814 Intermediate Similarity NPC269318
0.814 Intermediate Similarity NPC475270
0.814 Intermediate Similarity NPC475327
0.814 Intermediate Similarity NPC238056
0.814 Intermediate Similarity NPC476087
0.814 Intermediate Similarity NPC297768
0.814 Intermediate Similarity NPC173328
0.814 Intermediate Similarity NPC186992
0.814 Intermediate Similarity NPC475667
0.8095 Intermediate Similarity NPC474003
0.7955 Intermediate Similarity NPC60849
0.7955 Intermediate Similarity NPC477332
0.7955 Intermediate Similarity NPC472352
0.7907 Intermediate Similarity NPC294748
0.7907 Intermediate Similarity NPC146992
0.7907 Intermediate Similarity NPC477344
0.7907 Intermediate Similarity NPC158302
0.7907 Intermediate Similarity NPC85759
0.7907 Intermediate Similarity NPC477346
0.7907 Intermediate Similarity NPC22742
0.7865 Intermediate Similarity NPC473791
0.7831 Intermediate Similarity NPC291228
0.7831 Intermediate Similarity NPC206823
0.7831 Intermediate Similarity NPC308096
0.7791 Intermediate Similarity NPC475616
0.7727 Intermediate Similarity NPC183888
0.7727 Intermediate Similarity NPC224953
0.7727 Intermediate Similarity NPC143421
0.7727 Intermediate Similarity NPC119583
0.7727 Intermediate Similarity NPC472203
0.7727 Intermediate Similarity NPC472201
0.7727 Intermediate Similarity NPC89843
0.7727 Intermediate Similarity NPC126685
0.7727 Intermediate Similarity NPC27289
0.7727 Intermediate Similarity NPC44782
0.7727 Intermediate Similarity NPC472205
0.7727 Intermediate Similarity NPC477319
0.7727 Intermediate Similarity NPC472204
0.7727 Intermediate Similarity NPC184915
0.7727 Intermediate Similarity NPC477317
0.7727 Intermediate Similarity NPC472202
0.7727 Intermediate Similarity NPC115013
0.7727 Intermediate Similarity NPC259294
0.7727 Intermediate Similarity NPC290012
0.7727 Intermediate Similarity NPC307400
0.7727 Intermediate Similarity NPC123204
0.7727 Intermediate Similarity NPC472200
0.7727 Intermediate Similarity NPC477331
0.7727 Intermediate Similarity NPC477318
0.7727 Intermediate Similarity NPC169345
0.7711 Intermediate Similarity NPC184550
0.7711 Intermediate Similarity NPC185419
0.7692 Intermediate Similarity NPC470657
0.7692 Intermediate Similarity NPC312498
0.7692 Intermediate Similarity NPC473849
0.7619 Intermediate Similarity NPC225748
0.7619 Intermediate Similarity NPC9763
0.7619 Intermediate Similarity NPC169085
0.7619 Intermediate Similarity NPC163812
0.7619 Intermediate Similarity NPC39266
0.7614 Intermediate Similarity NPC267592
0.7609 Intermediate Similarity NPC31349
0.7582 Intermediate Similarity NPC478111
0.7558 Intermediate Similarity NPC477350
0.7547 Intermediate Similarity NPC308858
0.7547 Intermediate Similarity NPC475537
0.7527 Intermediate Similarity NPC470009
0.7525 Intermediate Similarity NPC470519
0.7525 Intermediate Similarity NPC231271
0.7476 Intermediate Similarity NPC207693
0.7471 Intermediate Similarity NPC244002
0.7471 Intermediate Similarity NPC476782
0.7471 Intermediate Similarity NPC216883
0.7471 Intermediate Similarity NPC476783
0.7471 Intermediate Similarity NPC476781
0.747 Intermediate Similarity NPC241265
0.747 Intermediate Similarity NPC211428
0.747 Intermediate Similarity NPC285003
0.7451 Intermediate Similarity NPC478038
0.7444 Intermediate Similarity NPC248415
0.7439 Intermediate Similarity NPC469925
0.7404 Intermediate Similarity NPC313668
0.7404 Intermediate Similarity NPC22709
0.7404 Intermediate Similarity NPC315836
0.7386 Intermediate Similarity NPC146380
0.7386 Intermediate Similarity NPC477326
0.7386 Intermediate Similarity NPC477320
0.7386 Intermediate Similarity NPC109887
0.7386 Intermediate Similarity NPC477328
0.7386 Intermediate Similarity NPC477323
0.7386 Intermediate Similarity NPC475425
0.7386 Intermediate Similarity NPC477329
0.7386 Intermediate Similarity NPC477330
0.7386 Intermediate Similarity NPC477325
0.7386 Intermediate Similarity NPC281563
0.7386 Intermediate Similarity NPC113745
0.7379 Intermediate Similarity NPC176756
0.7379 Intermediate Similarity NPC469787
0.7379 Intermediate Similarity NPC290247
0.7379 Intermediate Similarity NPC469788
0.7374 Intermediate Similarity NPC274695
0.7353 Intermediate Similarity NPC267637
0.7353 Intermediate Similarity NPC469827
0.7349 Intermediate Similarity NPC50228
0.7349 Intermediate Similarity NPC97736
0.734 Intermediate Similarity NPC471221
0.7333 Intermediate Similarity NPC470622
0.7327 Intermediate Similarity NPC80640
0.7326 Intermediate Similarity NPC125164
0.7308 Intermediate Similarity NPC224414
0.7308 Intermediate Similarity NPC469826
0.7308 Intermediate Similarity NPC167044
0.7284 Intermediate Similarity NPC314103
0.7282 Intermediate Similarity NPC184805
0.7282 Intermediate Similarity NPC166079
0.7282 Intermediate Similarity NPC306776
0.7282 Intermediate Similarity NPC273189
0.7245 Intermediate Similarity NPC215570
0.7238 Intermediate Similarity NPC217041
0.7229 Intermediate Similarity NPC477759
0.7229 Intermediate Similarity NPC477754
0.7229 Intermediate Similarity NPC286842
0.7229 Intermediate Similarity NPC477761
0.7229 Intermediate Similarity NPC206601
0.7229 Intermediate Similarity NPC477760
0.7229 Intermediate Similarity NPC477758
0.7228 Intermediate Similarity NPC162024
0.7222 Intermediate Similarity NPC79193
0.7212 Intermediate Similarity NPC126753
0.7212 Intermediate Similarity NPC471430
0.7209 Intermediate Similarity NPC51249
0.7209 Intermediate Similarity NPC475260
0.7209 Intermediate Similarity NPC475232
0.7209 Intermediate Similarity NPC473699
0.7209 Intermediate Similarity NPC474100
0.7209 Intermediate Similarity NPC473775
0.7204 Intermediate Similarity NPC51267
0.7196 Intermediate Similarity NPC157571
0.7188 Intermediate Similarity NPC470114
0.7184 Intermediate Similarity NPC100078
0.7172 Intermediate Similarity NPC475785
0.7172 Intermediate Similarity NPC475765
0.717 Intermediate Similarity NPC182185
0.717 Intermediate Similarity NPC106760
0.7158 Intermediate Similarity NPC221993
0.7157 Intermediate Similarity NPC244969
0.7157 Intermediate Similarity NPC227622
0.7157 Intermediate Similarity NPC213528
0.7143 Intermediate Similarity NPC67099
0.7143 Intermediate Similarity NPC250619
0.7143 Intermediate Similarity NPC475298
0.7143 Intermediate Similarity NPC473771
0.7143 Intermediate Similarity NPC475275
0.7129 Intermediate Similarity NPC80417
0.7115 Intermediate Similarity NPC41674
0.7115 Intermediate Similarity NPC469441
0.7115 Intermediate Similarity NPC228311
0.7108 Intermediate Similarity NPC477756
0.7108 Intermediate Similarity NPC477764
0.7108 Intermediate Similarity NPC477752
0.7108 Intermediate Similarity NPC315525
0.7108 Intermediate Similarity NPC135043
0.7108 Intermediate Similarity NPC477751
0.7103 Intermediate Similarity NPC272242
0.7103 Intermediate Similarity NPC469824
0.71 Intermediate Similarity NPC278028
0.71 Intermediate Similarity NPC328180
0.7097 Intermediate Similarity NPC115995
0.7091 Intermediate Similarity NPC179429
0.7075 Intermediate Similarity NPC87393
0.7075 Intermediate Similarity NPC469825
0.7065 Intermediate Similarity NPC100366
0.7065 Intermediate Similarity NPC242771
0.7065 Intermediate Similarity NPC164289
0.7065 Intermediate Similarity NPC311642
0.7041 Intermediate Similarity NPC478037
0.7041 Intermediate Similarity NPC478036
0.7041 Intermediate Similarity NPC475307
0.7037 Intermediate Similarity NPC98870
0.7019 Intermediate Similarity NPC114365
0.7019 Intermediate Similarity NPC154962
0.7019 Intermediate Similarity NPC177518
0.7019 Intermediate Similarity NPC123070
0.7019 Intermediate Similarity NPC18044
0.7019 Intermediate Similarity NPC88890
0.7019 Intermediate Similarity NPC18433
0.7019 Intermediate Similarity NPC169089
0.7019 Intermediate Similarity NPC132304
0.7009 Intermediate Similarity NPC471431
0.7009 Intermediate Similarity NPC66513
0.7 Intermediate Similarity NPC238796
0.7 Intermediate Similarity NPC475525
0.7 Intermediate Similarity NPC237071
0.7 Intermediate Similarity NPC475490
0.7 Intermediate Similarity NPC203434
0.7 Intermediate Similarity NPC475241

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC51662 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.7157 Intermediate Similarity NPD8138 Approved
0.7157 Intermediate Similarity NPD8082 Approved
0.7157 Intermediate Similarity NPD8086 Approved
0.7157 Intermediate Similarity NPD8083 Approved
0.7157 Intermediate Similarity NPD8085 Approved
0.7157 Intermediate Similarity NPD8139 Approved
0.7157 Intermediate Similarity NPD8084 Approved
0.7087 Intermediate Similarity NPD8275 Approved
0.7087 Intermediate Similarity NPD8276 Approved
0.7019 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD8081 Approved
0.7019 Intermediate Similarity NPD4056 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD4057 Clinical (unspecified phase)
0.6952 Remote Similarity NPD8393 Approved
0.6944 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6887 Remote Similarity NPD8140 Approved
0.6887 Remote Similarity NPD8307 Discontinued
0.6759 Remote Similarity NPD8305 Approved
0.6759 Remote Similarity NPD8306 Approved
0.6739 Remote Similarity NPD7329 Approved
0.6697 Remote Similarity NPD8087 Discontinued
0.6696 Remote Similarity NPD8269 Approved
0.6696 Remote Similarity NPD8266 Approved
0.6696 Remote Similarity NPD8268 Approved
0.6696 Remote Similarity NPD8267 Approved
0.6667 Remote Similarity NPD7909 Approved
0.6667 Remote Similarity NPD8133 Approved
0.6632 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6632 Remote Similarity NPD3669 Approved
0.663 Remote Similarity NPD4238 Approved
0.663 Remote Similarity NPD4802 Phase 2
0.6591 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6552 Remote Similarity NPD8517 Approved
0.6552 Remote Similarity NPD8513 Phase 3
0.6552 Remote Similarity NPD8515 Approved
0.6552 Remote Similarity NPD8516 Approved
0.6535 Remote Similarity NPD8171 Discontinued
0.6491 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6466 Remote Similarity NPD8346 Approved
0.6466 Remote Similarity NPD8347 Approved
0.6466 Remote Similarity NPD8345 Approved
0.6421 Remote Similarity NPD1779 Approved
0.6421 Remote Similarity NPD1780 Approved
0.6364 Remote Similarity NPD6686 Approved
0.6355 Remote Similarity NPD8300 Approved
0.6355 Remote Similarity NPD8301 Approved
0.6348 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6306 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6275 Remote Similarity NPD7983 Approved
0.6271 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6264 Remote Similarity NPD3181 Approved
0.625 Remote Similarity NPD898 Approved
0.625 Remote Similarity NPD896 Approved
0.625 Remote Similarity NPD897 Approved
0.6218 Remote Similarity NPD8080 Discontinued
0.6207 Remote Similarity NPD9496 Clinical (unspecified phase)
0.618 Remote Similarity NPD229 Approved
0.6176 Remote Similarity NPD6698 Approved
0.6176 Remote Similarity NPD46 Approved
0.6173 Remote Similarity NPD3728 Approved
0.6173 Remote Similarity NPD3730 Approved
0.6148 Remote Similarity NPD8074 Phase 3
0.6126 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6111 Remote Similarity NPD1700 Approved
0.6075 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6071 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6033 Remote Similarity NPD8328 Phase 3
0.6024 Remote Similarity NPD2267 Suspended
0.6022 Remote Similarity NPD1811 Approved
0.6022 Remote Similarity NPD1810 Approved
0.6 Remote Similarity NPD8392 Approved
0.6 Remote Similarity NPD8391 Approved
0.6 Remote Similarity NPD8390 Approved
0.5984 Remote Similarity NPD8341 Approved
0.5984 Remote Similarity NPD8299 Approved
0.5984 Remote Similarity NPD8340 Approved
0.5984 Remote Similarity NPD8342 Approved
0.5982 Remote Similarity NPD6412 Phase 2
0.5938 Remote Similarity NPD6115 Approved
0.5938 Remote Similarity NPD6697 Approved
0.5938 Remote Similarity NPD6118 Approved
0.5938 Remote Similarity NPD6114 Approved
0.5935 Remote Similarity NPD8451 Approved
0.593 Remote Similarity NPD6123 Approved
0.592 Remote Similarity NPD7319 Approved
0.5888 Remote Similarity NPD7839 Suspended
0.5887 Remote Similarity NPD7078 Approved
0.5887 Remote Similarity NPD8448 Approved
0.5887 Remote Similarity NPD8293 Discontinued
0.5854 Remote Similarity NPD7492 Approved
0.5847 Remote Similarity NPD6940 Discontinued
0.584 Remote Similarity NPD7736 Approved
0.5833 Remote Similarity NPD6116 Phase 1
0.5816 Remote Similarity NPD6928 Phase 2
0.5814 Remote Similarity NPD3198 Approved
0.5806 Remote Similarity NPD7507 Approved
0.5806 Remote Similarity NPD6616 Approved
0.5789 Remote Similarity NPD3702 Approved
0.5785 Remote Similarity NPD6059 Approved
0.5785 Remote Similarity NPD8377 Approved
0.5785 Remote Similarity NPD8294 Approved
0.5785 Remote Similarity NPD6054 Approved
0.5783 Remote Similarity NPD3729 Clinical (unspecified phase)
0.5772 Remote Similarity NPD7829 Approved
0.5772 Remote Similarity NPD7830 Approved
0.5769 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5769 Remote Similarity NPD6101 Approved
0.5738 Remote Similarity NPD8380 Approved
0.5738 Remote Similarity NPD8296 Approved
0.5738 Remote Similarity NPD8379 Approved
0.5738 Remote Similarity NPD8335 Approved
0.5738 Remote Similarity NPD8378 Approved
0.573 Remote Similarity NPD371 Approved
0.5729 Remote Similarity NPD6117 Approved
0.5701 Remote Similarity NPD5282 Discontinued
0.57 Remote Similarity NPD7345 Approved
0.5699 Remote Similarity NPD2686 Approved
0.5699 Remote Similarity NPD2687 Approved
0.5699 Remote Similarity NPD2254 Approved
0.5691 Remote Similarity NPD6370 Approved
0.5684 Remote Similarity NPD6113 Clinical (unspecified phase)
0.5663 Remote Similarity NPD890 Clinical (unspecified phase)
0.5663 Remote Similarity NPD893 Approved
0.5663 Remote Similarity NPD891 Phase 3
0.5663 Remote Similarity NPD894 Approved
0.5663 Remote Similarity NPD889 Approved
0.5663 Remote Similarity NPD887 Approved
0.5663 Remote Similarity NPD892 Phase 3
0.5663 Remote Similarity NPD895 Approved
0.5663 Remote Similarity NPD888 Phase 3
0.566 Remote Similarity NPD6411 Approved
0.5618 Remote Similarity NPD8961 Approved
0.561 Remote Similarity NPD8444 Approved
0.561 Remote Similarity NPD8033 Approved
0.561 Remote Similarity NPD6921 Approved
0.561 Remote Similarity NPD6015 Approved
0.561 Remote Similarity NPD6016 Approved
0.5607 Remote Similarity NPD5779 Approved
0.5607 Remote Similarity NPD5778 Approved
0.5606 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5603 Remote Similarity NPD4061 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   34230
ChEMBL   CHEMBL405862
ZINC  

Physicochemical Properties

Molecular Weight:  724.48
ALogP:  -1.3444
MLogP:  4.65
XLogP:  4.727
# Rotatable Bonds:  22
Polar Surface Area:  142.37
# H-Bond Aceptor:  11
# H-Bond Donor:  3
# Rings:  6
# Heavy Atoms:  51

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs